A one-pot synthesis of 3-nitrothiophene and 3-nitro-2-substituted thiophenes

McNabola, Neasa; O'Connor, Cornelius J.; Roydhouse, Mark D.; Wall, Michael; Southern, J. Mike

doi:10.1016/j.tet.2015.05.032

Cited by 14 publications

(2 citation statements)

References 25 publications

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“…噻吩是一种重要的杂环化合物, 存在于许多具有生物活性的化合物中. 2015 年, Southern 课题组 [101] 发展了在三乙胺存在下, 1,4-二噻烷-2,5-二醇与硝基苯乙烯一锅法合成 3-硝基-2-取代噻吩的反应, 同时优化了后处理步骤, 避免了色谱纯化(Eq. 53).…”

Section: 取代反应unclassified

Research Progress on Reactions Involving β-Nitrostyrene

Li,

Sun,

Zhao

et al. 2023

Chinese Journal of Organic Chemistry

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β-Nitrostyrene has a variety of biological activities and is also an important intermediate in organic synthesis, which can participate in a variety of chemical reactions due to its active chemical properties, and has attracted extensive attention from researchers. The reactions involving nitrostyrene compounds in recent years are summarized, and the reaction are divided into denitrification reactions and carbon-carbon double bonds according to reaction sites, expecting to provide a reference for new reactions with β-nitrostyrene compounds as substrates. Keywords β-nitrostyrene; denitrogenation reaction; carbon carbon double bond reaction β-硝基苯乙烯是重要的有机化合物, 广泛存在于具有多种生物活性的化合物结构和药物分子中, 其本身也具有抑制人端粒酶 [1] 、杀菌 [2][3] 及抗肿瘤 [4][5] 等活性. 近年来, 其在有机合成方向的应用也越来越被重视.

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Section: 取代反应unclassified

Research Progress on Reactions Involving β-Nitrostyrene

Li,

Sun,

Zhao

et al. 2023

Chinese Journal of Organic Chemistry

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“…[4] A simple workup procedure removes the requirement for purification by chromatography in most cases. [4,47] Conversion to the desired thiophenes was achieved in 98 % yield after heating at reflux for 24 h in the presence of silica gel (8 equiv., w/w), DDQ (4 equiv.) [4,47] Conversion to the desired thiophenes was achieved in 98 % yield after heating at reflux for 24 h in the presence of silica gel (8 equiv., w/w), DDQ (4 equiv.)…”

Section: Synthesis Of Thiophenesmentioning

confidence: 99%

1,4‐Dithiane‐2,5‐diol: An Attractive Platform for the Synthesis of Sulfur‐Containing Functionalized Heterocycles

2018

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This microreview highlights the utility of 1,4‐dithiane‐2,5‐diol (1) as a source for the in situ generation of 2‐mercaptoacetaldehyde (2), a versatile two‐carbon synthon featuring both electrophilic and nucleophilic reaction centres and widely utilized as an attractive platform for the preparation of sulfur‐containing molecules. We discuss the chemistry involved, mainly focusing on its applications to the construction of sulfur‐containing heterocyclic compounds including the thiophene and 1,3‐thiazole families and other different sulfur–nitrogen and sulfur–oxygen heterocycles that continue to be a pillar of organic synthesis as a result of their broad application in organic and medicinal chemistry.

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